This invention relates to antibiotic derivatives of apramycin and intermediates and starting materials in the synthesis therefor. In particular, it relates to antibiotic derivatives of apramycin wherein the 6"-hydroxyl group is replaced by hydrogen, C.sub.1 to C.sub.3 -alkylsulfonyloxy, phenylsulfonyloxy, substituted phenylsulfonyloxy, tert-butyldimethylsilyloxy, fluoro, chloro, bromo, iodo, azido, amino, C.sub.1 to C.sub.3 -alkylthio, phenylthio, cyano or aminomethyl.
Apramycin is used as a veterinary antibiotic (see U.S. Pat. Nos. 3,691,279, 3,853,709 and 3,876,767) and has the following structure: ##STR1##
It is known in the aminoglycoside art that substitution on various positions of the aminoglycoside rings may increase the activity of the parent aminoglycoside. Some recent substituted-apramycin derivatives, in which the 1, 3 and 2'-amino groups were functionalized, have been reported by Herbert A. Kirst, Brenda A. Truedell and John E. Toth in Tetrahedron Letters, vol. 22, pp 295-298 (1981).
The apramycin derivatives of the instant application are substituted at the 6"-position as specified and possess broad-spectrum antibiotic activity while differing in structure from the aforementioned compounds and other compounds previously disclosed in the art.